IP Library Granted Patent US 9,238,712
Granted Patent B2
US 9,238,712 · App. 13/827,155 · Granted Jan 19, 2016

Tagged polymers and methods of use

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Quick Facts
Patent No.
US 9,238,712
App. No.
13/827,155
Granted
Jan 19, 2016
Kind
B2
Abstract

A polymer includes a monomeric repeat unit represented by Formula I: In Formula I, R 1 is alkyl, alkenyl, alkynyl, aryl, heteroaryl, cycloalkyl, or heterocyclyl; R 2 is alkyl, haloalkyl, alkenyl, alkynyl; R 3 is alkyl, OH, halo, or alkoxy; R 4 is alkyl, OH, halo, or alkoxy; Y is absent, C(O), C 1 -C 4 alkylidene, or C 1 -C 4 alkylideneamino; L is alkylidene, alkylidene-O-alkylidene, alkylidene-S-alkylidene, alkenylidene, cycloalkylidene, arylene, heteroarylene, C(O)O, or C(O)S; n1 is 0, 1, 2, 3, or 4; and n2 is 0, 1, 2, 3, or 4.

Claims (52)

1. A polymer comprising a monomeric repeat unit represented by Formula I:

wherein:

R 1 is alkenyl, alkynyl, aryl, heteroaryl, cycloalkyl, or heterocyclyl;

R 2 is alkyl, haloalkyl, alkenyl, or alkynyl;

R 3 is alkyl, OH, halo, or alkoxy;

R 4 is alkyl, OH, halo, or alkoxy;

Y is absent, C(O), C 1 -C 4 alkylidene, or C 1 -C 4 alkylideneamino;

L is alkylidene, alkylidene-O-alkylidene, alkylidene-S-alkylidene, alkenylidene, cycloalkylidene, arylene, heteroarylene, C(O)O, or C(O)S;

n1 is 0, 1, 2, 3, or 4; and

n2 is 0, 1, 2, 3, or 4.

2. The polymer of claim 1 , wherein the monomeric repeat unit is represented by Formula IA:

wherein:

Z 1 is absent, CO, SO 2 , a residue derived from an acrylate, or a residue derived from an epoxide; and

Z 2 is absent, CO, SO 2 , a residue derived from an acrylate, or a residue derived from an epoxide.

3. The polymer of claim 1 , wherein the monomeric repeat unit is

4. The polymer of claim 1 , wherein the monomeric repeat unit is

5. The polymer of claim 1 , wherein R 1 is a chromophore, or fluorophore, or wherein R 1 contains a radioisotope.

6. The polymer of claim 1 , wherein R 4 is halo.

7. A polymer represented by Formula II:

wherein:

R 1 is alkyl, alkenyl, alkynyl, aryl, heteroaryl, cycloalkyl, or heterocyclyl;

R 2 is alkyl;

R 5 , R 6 , R 7 , and R 8 are independently H or alkyl;

Y is absent, C(O), C 1 -C 4 alkylidene, or C 1 -C 4 alkylideneamino;

L is alkylidene, alkylidene-O-alkylidene, alkylidene-S-alkylidene, alkenylidene, cycloalkylidene, arylene, heteroarylene, C(O)O, or C(O)S; and

m, p, and q are independently an integer of 1 to 10,000.

8. The polymer of claim 7 , wherein the polymer is represented by Formula III:

9. The polymer of claim 7 , wherein R 5 , R 6 , R 7 , and R 8 are H.

10. The polymer of claim 7 , wherein L is —CH 2 CH 2 —.

11. The polymer of claim 7 , wherein Y is absent.

12. The polymer of claim 7 , wherein Y is C(O).

13. The polymer of claim 7 , wherein Y is —(C 1 -C 4 alkylidene)-N(C 1 -C 4 alkyl)-.

14. The polymer of claim 13 , wherein Y is —CH 2 CH 2 —N(CH 2 CH 3 )—.

15. The polymer of claim 7 , wherein R 1 is alkyl.

16. The polymer of claim 15 , wherein R 1 is 13 CH 3 .

17. The polymer of claim 7 , wherein R 1 is

18. The polymer of claim 7 , wherein R 1 is

19. The polymer of claim 7 , wherein R 1 is

20. A method of preparing a polymer, the method comprising:

contacting a compound of Formula IV with a compound of Formula V

to form a compound of Formula VI

and

contacting the compound of Formula VI with a linking compound to form the polymer, wherein the linking compound comprises OC(O)O, SO 2 , or an epoxide and the polymer comprises a monomeric repeat unit represented by Formula I

wherein:

R 1 is alkenyl, alkynyl, aryl, heteroaryl, cycloalkyl, or heterocyclyl;

R 2 is alkyl;

R 3 is alkyl, OH, halo, or alkoxy;

R 4 is alkyl, OH, halo, or alkoxy;

Y is absent, C(O), C 1 -C 4 alkylidene, or C 1 -C 4 alkylideneamino;

L is alkylidene, alkylidene-O-alkylidene, alkylidene-S-alkylidene, alkenylidene, cycloalkylidene, arylene, heteroarylene, C(O)O, or C(O)S;

n1 is 0, 1, 2, 3, or 4; and

n2 is 0, 1, 2, 3, or 4.

Assignments (4)
SECURITY INTEREST Recorded Jan 29, 2019
From: EMPIRE TECHNOLOGY DEVELOPMENT LLC
To: CRESTLINE DIRECT FINANCE, L.P.
Reel/Frame 048373/0217 →
ASSIGNMENT OF ASSIGNOR'S INTEREST Recorded Jul 1, 2015
From: CARLSON, WILLIAM BRENDEN; PHELAN, GREGORY DAVID
To: SEATTLE POLYMER COMPANY
Reel/Frame 036001/0047 →
ASSIGNMENT OF ASSIGNOR'S INTEREST Recorded Jul 1, 2015
From: CASASANTA, VINCENZO, III
To: EMPIRE TECHNOLOGY DEVELOPMENT LLC
Reel/Frame 036001/0083 →
ASSIGNMENT OF ASSIGNOR'S INTEREST Recorded Jul 1, 2015
From: SEATTLE POLYMER COMPANY
To: EMPIRE TECHNOLOGY DEVELOPMENT LLC
Reel/Frame 036001/0099 →